ETHYLMORPHINE

US Previously Marketed

First marketed in 1921

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H23NO3
Molecular Weight	313.3908
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12OC3=C4C(C[C@@]5([H])N(C)CC[C@@]14[C@@]5([H])C=C[C@@H]2O)=CC=C3OCC

InChI

InChIKey=OGDVEMNWJVYAJL-LEPYJNQMSA-N

InChI=1S/C19H23NO3/c1-3-22-15-7-4-11-10-13-12-5-6-14(21)18-19(12,8-9-20(13)2)16(11)17(15)23-18/h4-7,12-14,18,21H,3,8-10H2,1-2H3/t12-,13+,14-,18-,19-/m0/s1

HIDE SMILES / InChI

Description
Sources: http://www.bepharbel.com/uploads/produits_rcp/4yo9nqr3lf_be-spc-en-codethyline-clean.pdf

Ethylmorphine is a derivative of morphine with analgesic and antitussive effect. It acts by activating the opioid receptors and thus has a direct influence on the CNS system. Ethylmorphine was approved in Europe for the treatment of dry cough (Codethyline, Dionine).

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Opioid receptors; mu/kappa/delta 33 Target ID: CHEMBL2095181 Sources: http://www.bepharbel.com/uploads/produits_rcp/4yo9nqr3lf_be-spc-en-codethyline-clean.pdf	Agonist 2678		345.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cough 106 Sources: http://www.bepharbel.com/uploads/pdf/qltj3rob2v_DH_V04_INSERT-CODETHYLINE-MEDISPEHERE-FR.pdf	Primary		Approved 8429	CODETHYLINE Approved Use A cough medicine.

C_max

Value	Dose	Co-administered	Analyte	Population
1.09 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7654478	1.5 mg/kg bw single, oral dose: 1.5 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered:		ETHYLMORPHINE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
222 μM × min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7654478	1.5 mg/kg bw single, oral dose: 1.5 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered:		ETHYLMORPHINE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.97 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7654478	1.5 mg/kg bw single, oral dose: 1.5 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered:		ETHYLMORPHINE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
8.5 mg single, oral Dose: 8.5 mg Route: oral Route: single Dose: 8.5 mg Sources: https://pubmed.ncbi.nlm.nih.gov/20158595	healthy, 10 months n = 1 Health Status: healthy Age Group: 10 months Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/20158595	Other AEs: Sedation... Other AEs: Sedation (grade 5) Sources: https://pubmed.ncbi.nlm.nih.gov/20158595
1.5 mg/kg single, oral Dose: 1.5 mg/kg Route: oral Route: single Dose: 1.5 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/7654478	healthy, 24 years n = 10 Health Status: healthy Age Group: 24 years Sex: M Population Size: 10 Sources: https://pubmed.ncbi.nlm.nih.gov/7654478	Other AEs: Dizziness, Drowsiness... Other AEs: Dizziness (7 patients) Drowsiness (slight, 2 patients) Loose stools (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/7654478

AEs

AE	Significance	Dose	Population
Sedation	grade 5	8.5 mg single, oral Dose: 8.5 mg Route: oral Route: single Dose: 8.5 mg Sources: https://pubmed.ncbi.nlm.nih.gov/20158595	healthy, 10 months n = 1 Health Status: healthy Age Group: 10 months Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/20158595
Loose stools	1 patient	1.5 mg/kg single, oral Dose: 1.5 mg/kg Route: oral Route: single Dose: 1.5 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/7654478	healthy, 24 years n = 10 Health Status: healthy Age Group: 24 years Sex: M Population Size: 10 Sources: https://pubmed.ncbi.nlm.nih.gov/7654478
Dizziness	7 patients	1.5 mg/kg single, oral Dose: 1.5 mg/kg Route: oral Route: single Dose: 1.5 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/7654478	healthy, 24 years n = 10 Health Status: healthy Age Group: 24 years Sex: M Population Size: 10 Sources: https://pubmed.ncbi.nlm.nih.gov/7654478
Drowsiness	slight, 2 patients	1.5 mg/kg single, oral Dose: 1.5 mg/kg Route: oral Route: single Dose: 1.5 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/7654478	healthy, 24 years n = 10 Health Status: healthy Age Group: 24 years Sex: M Population Size: 10 Sources: https://pubmed.ncbi.nlm.nih.gov/7654478

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737		substrate 1217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2D6 1217	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/7756104/ \| https://pubmed.ncbi.nlm.nih.gov/7654478/	yes
CYP3A4 1737	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/7756104/	yes

Sourcing

Vendor/Aggregator	ID	URL
ABI Chem	AC1Q37UW
Ambinter	Amb22801513	http://www.ambinter.com/reference/22801513
Angene	AGN-PC-0OHUE6
Aurora Fine Chemicals LLC	A17.879.672	http://online.aurorafinechemicals.com/info?ID=A17.879.672
ChemMol	99147254	http://www.chemmol.com/chemmol/99147254.html
Chemieliva Pharmaceutical Co., Ltd	PBCM1411510
Compound Cloud	23724836
Compound Cloud	5359271
Debye Scientific	DB-056088
Glentham Life Sciences	GP3600	http://www.glentham.com/products/product/GP3600/
LGC Standards	LGCAMP0799.07-01	https://www.lgcstandards.com/US/en/p/LGCAMP0799.07-01
LGC Standards	LGCFOR0799.07	https://www.lgcstandards.com/US/en/p/LGCFOR0799.07
LGC Standards	MM0799.07	https://www.lgcstandards.com/US/en/p/MM0799.07
NovoSeek	5359271
Sigma Aldrich	E-052
Sigma Aldrich	E8512
Sigma Aldrich	E8512\|SIGMA
Sigma-Aldrich	E-052_CERILLIAN	https://www.sigmaaldrich.com/catalog/product/cerillian/e052?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	E8512_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/e8512?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S620625	https://www.smolecule.com/products/s620625
Tetrahedron	TS61083
ZINC	ZINC000003629718	http://zinc15.docking.org/substances/ZINC000003629718
eMolecules	193735204

PubMed

Title	Date	PubMed
[Experimental study on using diclofenac sodium or dionine topically to treat fibrinous membrane after intraocular lens implantation].	2001 Jun 28	12536684
Effects of fumonisin B1 present in Fusarium moniliforme culture material on drug metabolising enzyme activities in ducks.	2001 May 19	11369472
Evidence for the presence of active cytochrome P450 systems in Schistosoma mansoni and Schistosoma haematobium adult worms.	2002 May 22	12023046
Interpretation of the presence of 6-monoacetylmorphine in the absence of morphine-3-glucuronide in urine samples: evidence of heroin abuse.	2003 Oct	14508389
Genomic characterization and regulation of CYP3a13: role of xenobiotics and nuclear receptors.	2003 Sep	12958193
Expression and characterization of human cytochrome P450 4F11: Putative role in the metabolism of therapeutic drugs and eicosanoids.	2004 Sep 15	15364545
Inhibition of rat liver CYP2D in vitro and after 1-day and long-term exposure to neuroleptics in vivo-possible involvement of different mechanisms.	2005 Jan	15572279
[Current problems in the quality control of pharmaceutical preparations manufactured in pharmacies II. Paracetamol contraining preparations].	2006	17575797
Electrospray LC-MS method with solid-phase extraction for accurate determination of morphine-, codeine-, and ethylmorphine-glucuronides and 6-acetylmorphine in urine.	2007 Mar	17536742
A hybrid FIA/HPLC system incorporating monolithic column chromatography.	2007 Sep 26	17903475
[Study of cytotoxic and antiviral effects of some eye drops].	2008	19354165
Determining plasma morphine levels using GC-MS after solid phase extraction to monitor drug levels in the postoperative period.	2008 Jun	18568238
Error in the article: "driving under the influence of opiates: concentration relationships between morphine, codeine, 6-acetyl morphine, and ethyl morphine in blood".	2008 Jun	18544226
Driving under the influence of opiates: concentration relationships between morphine, codeine, 6-acetyl morphine, and ethyl morphine in blood.	2008 May	18430293
Simultaneous screening and quantification of 25 opioid drugs in post-mortem blood and urine by liquid chromatography-tandem mass spectrometry.	2009 Apr 15	19232849
Determination of opiates and cocaine in urine by high pH mobile phase reversed phase UPLC-MS/MS.	2009 Feb 1	19144579
Importance of using highly pure internal standards for successful liquid chromatography/tandem mass spectrometric bioanalytical assays.	2009 May	19308966
[Pharmacological treatment of acute cough].	2009 May 14	19448753
[The effect of warfarin was potentiated by an antitussive. Cocillana-Etyfin increased the PK(INR) value].	2009 Nov 4-12	19998819
Bovine liver slices combined with an androgen transcriptional activation assay: an in-vitro model to study the metabolism and bioactivity of steroids.	2010 May	20237917

Patents

Sample Use Guides

In Vivo Use Guide

The recommended dose in adults is 50 mg of codethyline per day, i.e. 10 tablets (1 tablet contains 5 mg of ethylmorphine hydrochloride) per day over several intakes, at a minimum of 4 hours apart. In children the normal dose is 1 tablet per intake, to be renewed after 6 hours if necessary, without exceeding 4 tablets per day.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Name

Type

Language

ETHYLMORPHINE

Common Name

English

Ethylmorphine [WHO-DD]

Common Name

English

IDS-NE-005(SECT.2)

Code

English

R05DA01

Code

English

CODETHYLINE

Common Name

English

3-ETHOXYMORPHINE

Common Name

English

ETHYLMORPHINE [MI]

Common Name

English

(5.ALPHA.,6.ALPHA.)-7,8-DIDEHYDRO-4,5-EPOXY-3-ETHOXY-17-METHYLMORPHINAN-6-OL

Systematic Name

English

Classification Tree Code System Code

WHO-VATC

QS01XA06